$130+ Cheap flights from Chicago (CHI) to Jamaica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Apr 14 — Apr 211
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Jamaica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Jamaica
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to JamaicaExplore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 15, 2026.
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 15, 2026.
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1210:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Wed 6/171:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 3/13![Southwest logo]()
$318
This American Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:45 am
ORD
- MBJ
Nonstop4h 16m
American Airlines
Tue 11/103:14 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 3/13![American Airlines logo]()
$318
This American Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sun 5/101:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 3/11![American Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 4/252:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 3/11![United Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sun 5/173:20 pm
MBJ
- ORD
1 stop8h 14m
American Airlines
Deal found 3/13![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:05 am
ORD
- MBJ
Nonstop4h 06m
American Airlines
Thu 3/1912:21 pm
MBJ
- ORD
1 stop21h 51m
American Airlines
Deal found 3/13![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Mon 5/1110:17 am
MBJ
- ORD
1 stop23h 54m
American Airlines
Deal found 3/13![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/64:05 pm
ORD
- MBJ
1 stop21h 03m
American Airlines
Thu 6/112:30 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 3/14![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:40 am
ORD
- MBJ
1 stop7h 35m
American Airlines
Sat 5/23:20 pm
MBJ
- ORD
1 stop16h 19m
American Airlines
Deal found 3/15![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sun 5/173:20 pm
MBJ
- ORD
1 stop8h 14m
American Airlines
Deal found 3/14![American Airlines logo]()
$338
This Priceline deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Wed 5/131:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/14![Frontier logo]()
$372
This Booking.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
- MBJ
1 stop21h 56m
Frontier
Mon 5/181:16 pm
MBJ
- MDW
1 stop21h 56m
Frontier
Deal found 3/13![Frontier logo]()
$397
Best flights from Chicago to JamaicaDiscover carefully curated flight deals from Chicago to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 15, 2026.
Discover carefully curated flight deals from Chicago to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 15, 2026.
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Thu 4/234:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/10![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- MBJ
1 stop5h 29m
Delta
Tue 5/121:18 pm
MBJ
- MDW
1 stop7h 51m
Delta
Deal found 3/10![Delta logo]()
$472
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:15 am
MDW
- MBJ
1 stop9h 05m
Southwest
Wed 5/1312:15 pm
MBJ
- MDW
2 stops10h 00m
Southwest
Deal found 3/14![Southwest logo]()
$478
This Cheapflightsfares deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- KIN
1 stop6h 30m
Spirit Airlines
Mon 4/273:18 pm
KIN
- ORD
1 stop18h 18m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$492
This Mytrip deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:55 am
ORD
- KIN
2 stops22h 21m
Multiple Airlines
Thu 4/2310:01 am
KIN
- ORD
2 stops25h 41m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$619
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 4/252:40 pm
MBJ
- ORD
1 stop8h 35m
United Airlines
Deal found 3/12![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Sat 6/134:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 3/13![United Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Tue 4/214:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/10![United Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:23 am
MDW
- MBJ
1 stop9h 11m
Delta
Wed 6/102:30 pm
MBJ
- MDW
1 stop7h 15m
Delta
Deal found 3/10![Delta logo]()
$472
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MDW
- MBJ
1 stop5h 35m
Southwest
Tue 5/512:15 pm
MBJ
- MDW
1 stop9h 10m
Southwest
Deal found 3/13![Southwest logo]()
$492
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 5/91:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/11![United Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:15 am
ORD
- KIN
1 stop11h 45m
Delta
Sat 4/259:00 am
KIN
- ORD
1 stop11h 16m
Delta
Deal found 3/11![Delta logo]()
$536
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:10 am
MDW
- MBJ
1 stop7h 20m
Southwest
Sat 4/2512:10 pm
MBJ
- MDW
1 stop10h 25m
Southwest
Deal found 3/12![Southwest logo]()
$552
This United Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 4/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/13![United Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:00 am
ORD
- KIN
2 stops13h 00m
Delta
Sat 5/29:00 am
KIN
- ORD
1 stop14h 59m
Delta
Deal found 3/11![Delta logo]()
$541
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Sat 5/91:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/11![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
MDW
- MBJ
1 stop6h 55m
Southwest
Tue 6/91:50 pm
MBJ
- MDW
Nonstop4h 00m
Southwest
Deal found 3/10![Southwest logo]()
$580
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:00 am
MDW
- MBJ
1 stop9h 25m
Delta
Thu 6/112:30 pm
MBJ
- MDW
1 stop7h 15m
Delta
Deal found 3/14![Delta logo]()
$547
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:35 pm
MDW
- MBJ
2 stops18h 00m
Southwest
Wed 4/2212:15 pm
MBJ
- MDW
1 stop7h 30m
Southwest
Deal found 3/11![Southwest logo]()
$582
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 4/252:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 3/10![United Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:23 am
MDW
- MBJ
1 stop9h 11m
Delta
Wed 6/31:18 pm
MBJ
- MDW
1 stop7h 51m
Delta
Deal found 3/15![Delta logo]()
$547
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:25 pm
ORD
- MBJ
1 stop24h 45m
United Airlines
Thu 4/161:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/10![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:35 pm
MDW
- MBJ
2 stops17h 20m
Southwest
Thu 6/42:20 pm
MBJ
- MDW
1 stop10h 20m
Southwest
Deal found 3/11![Southwest logo]()
$595
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:30 am
ORD
- KIN
1 stop14h 30m
Delta
Sat 4/189:00 am
KIN
- ORD
1 stop9h 48m
Delta
Deal found 3/15![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:35 pm
ORD
- MBJ
1 stop17h 35m
United Airlines
Sat 4/251:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/11![United Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:00 am
ORD
- KIN
2 stops13h 00m
Delta
Mon 5/49:00 am
KIN
- ORD
2 stops9h 52m
Delta
Deal found 3/13![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:10 am
ORD
- KIN
1 stop12h 50m
Delta
Tue 4/289:00 am
KIN
- ORD
1 stop7h 42m
Delta
Deal found 3/10![Delta logo]()
$606
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/119:30 am
ORD
- KIN
1 stop10h 30m
Delta
Wed 6/179:00 am
KIN
- ORD
1 stop11h 18m
Delta
Deal found 3/11![Delta logo]()
$606
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:19 am
ORD
- KIN
1 stop8h 41m
Delta
Tue 4/219:00 am
KIN
- ORD
2 stops9h 52m
Delta
Deal found 3/10![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:00 am
MDW
- KIN
1 stop14h 00m
Delta
Wed 6/179:00 am
KIN
- MDW
2 stops9h 31m
Delta
Deal found 3/14![Delta logo]()
$631
Last-minute flights from Chicago to JamaicaDiscover last-minute flight deals from Chicago to Jamaica. Data last updated March 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Jamaica. Data last updated March 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:05 am
ORD
- MBJ
Nonstop4h 06m
American Airlines
Thu 3/1912:21 pm
MBJ
- ORD
1 stop21h 51m
American Airlines
Deal found 3/13![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Thu 4/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/10![United Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:48 am
ORD
- MBJ
1 stop7h 42m
United Airlines
Sat 4/182:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 3/11![United Airlines logo]()
$348
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/128:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 4/161:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/11![United Airlines logo]()
$318
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:36 pm
ORD
- KIN
1 stop18h 59m
Spirit Airlines
Mon 4/273:18 pm
KIN
- ORD
1 stop18h 18m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Wed 4/224:12 pm
MBJ
- ORD
1 stop17h 26m
United Airlines
Deal found 3/10![United Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:48 am
ORD
- MBJ
1 stop7h 42m
United Airlines
Sat 4/252:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 3/12![United Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:46 pm
ORD
- MBJ
1 stop12h 27m
American Airlines
Tue 4/284:37 pm
MBJ
- ORD
1 stop20h 48m
American Airlines
Deal found 3/12![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Sun 5/310:17 am
MBJ
- ORD
1 stop7h 41m
American Airlines
Deal found 3/12![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Mon 5/410:17 am
MBJ
- ORD
1 stop22h 13m
American Airlines
Deal found 3/14![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:40 am
ORD
- MBJ
1 stop7h 35m
American Airlines
Sat 5/23:20 pm
MBJ
- ORD
1 stop16h 19m
American Airlines
Deal found 3/15![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:15 am
ORD
- MBJ
1 stop6h 10m
American Airlines
Mon 5/410:17 am
MBJ
- ORD
1 stop22h 13m
American Airlines
Deal found 3/13![American Airlines logo]()
$344
One-way flights from Chicago to JamaicaSearch for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
Search for one-way flight options from Chicago to Jamaica. Find affordable one-way fares based on user searches. Data last updated March 15, 2026.
This Priceline deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:05 am
ORD
- MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 3/15![American Airlines logo]()
$138
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:00 am
ORD
- MBJ
1 stop8h 25m
American Airlines
Deal found 3/15![American Airlines logo]()
$142
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:00 am
MDW
- MBJ
1 stop6h 55m
Southwest
Deal found 3/15![Southwest logo]()
$142
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 3/14![American Airlines logo]()
$143
This Super.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- MBJ
1 stop6h 00m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$144
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:00 am
ORD
- MBJ
1 stop8h 55m
American Airlines
Deal found 3/15![American Airlines logo]()
$147
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1210:05 am
MDW
- MBJ
Nonstop3h 50m
Southwest
Deal found 3/13![Southwest logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:45 pm
ORD
- MBJ
1 stop16h 31m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- MBJ
1 stop6h 00m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:10 pm
ORD
- KIN
1 stop17h 25m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$160
This Frontier deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:00 am
MDW
- MBJ
1 stop6h 42m
Frontier
Deal found 3/15![Frontier logo]()
$162
Find flight deals from Chicago to Jamaica
Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated March 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $318 (Southwest) |
One-way from | $130 (Priceline) |
Popular in | June |
Cheapest in | January |
Average price | $592 |
Good round-trip deal | $302 or less |
Good one-way deal | $132 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 15, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 4/8
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
Thu 4/23
4:12 pm-11:43 pm
1 stop7h 31m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 4/18
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 4/25
2:40 pm-11:15 pm
1 stop8h 35m
$348
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 6/6
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Sat 6/13
4:12 pm-11:26 pm
1 stop7h 14m
$371
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 4/15
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
Tue 4/21
4:12 pm-11:43 pm
1 stop7h 31m
$380
Quickest round-trip
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/2
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 5/9
1:52 pm-6:15 pm
Nonstop4h 23m
$428
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 4/20
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Thu 4/23
1:52 pm-6:15 pm
Nonstop4h 23m
$428
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 5/6
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
Sat 5/9
1:52 pm-6:15 pm
Nonstop4h 23m
$432
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 4/20
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 4/25
2:40 pm-12:45 am
1 stop10h 05m
$438
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 4/9
2:25 pm-3:10 pm
1 stop24h 45m
Montego Bay Sangster Intl
Thu 4/16
1:52 pm-6:15 pm
Nonstop4h 23m
$446
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 4/21
9:35 pm-3:10 pm
1 stop17h 35m
Montego Bay Sangster Intl
Sat 4/25
1:52 pm-6:15 pm
Nonstop4h 23m
$454
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
MDW-MBJ
ORD-MBJ
ORD-KIN
MDW-KIN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Jamaica
CHI-JM0
MDW-MBJ
ORD-MBJ
ORD-KIN
MDW-KIN
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $95). Flying from Chicago to Jamaica in August is currently the most expensive (average of $384). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to JM?
Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 15, 2026.
When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Chicago to Jamaica
Explore weekly flight availability from Chicago to Jamaica. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 15, 2026.
The most flights from CHI to JM0 are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated March 15, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Chicago to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jamaica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Jamaica by cabin class
Find flights from Chicago to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Jamaica flights
Browse other Chicago and Jamaica flight options. Last updated on March 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Jamaica flights
Consider these flights traveling from Chicago to Jamaica.
Top 6 airlines flying from Chicago to Jamaica
Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$453 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$144 | Average$672 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$302 | Average$547 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$375 | Average$672 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$518 | Average$683 | FlexibilityNo cancel fee | On-time63% |